Emulsion



retested a. 21, 1941' UNIT-En STATES PATENT OFFlCE y $2 232, I

No Drawing. Application January 24, 1940,

Serial No. 315,334 I This invention relates to the preparation ,ofmaterials which are readily dispersible or emulsifiable inor-wlth'aqueous media, as well as to the preparation of stabledispersions or emulsions, of the type comprising aqueous media andvoleaginous, resinous, or other waterrepelling materials. I

Emulsionsor dispersions of the character referred to have been preparedheretofore in which emulsifying or dispersing agents of numerous'typeshave been utilized. While the stability of these emulsions ordispersions is enhanced by the addition of said emulsifying ordispersing agents,

, still, in many instances, the improvements have .15

completely satisfactory solution to the problems not been sufficientlymarked so as to provide a confronting those versed in the art. 1

Among the numerous emulsifying or dispersing agents whose use has beensuggested for enhancing the stability of oleaginous-aqueous emulsionsare the higher molecular weight aliphatic alcohol sulphates andsulphonates, the sulphonated oils such as Turkey-red oil, the sulphatesand phosphates of higher fatty acid monoglycerides, monoglycerides anddiglycerides of higher molecular weight aliphatic, particularly, fattyacids,

and the like, 7

found to be fully satisfactory since, among other None of these agentshas been things, the emulsions, for example, tend to separate on more orless prolonged standing.

In accordance with the present invention, emulsions and dispersions ofexcellent character and stability are produced by utilizing certain'emul sifying agents, hereinafter defined and described in detail. Theseemulsifying agents, which are incorporated in the emulsions ordispersions in varying amounts, are reaction products or condensationproducts in the form of derivatives of hydroxy-alkyl amines.

amines with aliphatic carboxylic acids containpounds also including ahigher molecular weight lipophile group, particularly in aliphatic orfatty 45 7 acid acyl group. agents comprise or may be characterized asMore particularly, most of the amides of hydroxy-alkyl amines,especially secondary hydroxy-alkyl amines, with aliphatic lipophileradical containing at least eight carbon atoms.

Many of the agents which may be utilized for '65 In general, such agents4o or reaction products comprise amides of hydroxy,

ing not more than live carbon atoms, said com- 50 carbon atoms,

the purposes of the present invention fall wit the scope of the generalformula:

' D-(fl')s R "JN o \M-(OH), wherein 10 is an aliphatic acyl radicalcontaining not more than five carbon atoms, D and M are the same ordissimilar organic radicals containing at least two carbon atoms, R isan organic lipophile radical, and :c and 11 are small whole numbers, forexample, one or two. 1 A more limited aspect of the agents which areemployed in accordance with the present invention may be represented'bythe general formula O-alkylene): and (alkylene-S-alkyleneM where t and ware whole numbers, and R'is a lipophilic organic radical containing atleast eight carbon atoms.

A further and still more limited representation of agents used for thepurpose of the present invention, covering especially preferredembodiments, may be represented by the generalformula:

CH;I(CH:)O-CR"- is a fatty acid acyl radical containing not more thanlive carbon atoms and preferably only'tw'o is a fatty acid acyl radicalcontaining at least eight carbon atoms, and v and z are whole numbers.

The radical R in the above formulae may be of aliphatic,cycle-aliphatic, aromatic or ammatic-aliphatic character and may includesubstltuent groups such as amino, hydroxy, halogen, sulphate,sulphonate, phosphate, carbonyl, nitrlle. and the like, as-will bepointed out hereinafter but it is particularly preferred that-it beunsubstituted. aliphatic or fatty and contain at least eight andpreferably from twelve to eighteen carbon atoms. D, M, and alk,likewise, may contain substituent groups such as amino, hydroxy.halogen, sulphate, sulphonate, phosphate, carbonyl, nitrile, and thelike, and the sequence of carbon atoms therein may be interrupted by O,8, C=O, NH, NR where R is alkyl, and the like. It is especiallypreferred, however, that each of D. M and alk comprise unsubstitutedalkylene radicals containing from two to four carbon atoms.

In order that the nature. of the agents which are used for the purposesof the invention may become more apparent, there are listed hereinbelowrepresentative agents which fall within the scope of the presentinvention.

1 clIk-ca \CSHPOH o CHEW-70111! (3) CHr-Q- CsEs-OH C:Hr -C11Ha (a)cm-G-N g CsHr-OH o cmr-o- -cuna (4 cm-c- \CSHPOH o cinr-o-a-cuna (a)CHr-C- t cinron qnrcnr-cnr-o-cnfla (o) CHr-CHr-C- CHr-CHa-CH:OH

' CHr-CHa-CHr-O-Cufln (1) CHa-CHr-CHr-C-N CH.1CH:-CHrOH(CHflr-CHr-O-C-CuHn (abietie acid) 0 o cm-o-Ea-cm (11) OKscan-onHr-OOONa O cH-LN t m CrHrOH $00K (l3) CHs-C-N CsHr-OH Cs r-OHClHPO-CHHII (so) CHr-C-N A CsHn-OH CHr-CHr-CHr-CHr-OH CHr-C- (so) ICsHiOH CHs-C-NHO\ a l CsHcOH l CHaO H no-cm o cim-o- CnHu no-cm ooncine-on H H CsHcOH canon with or without diluents. It will furthermorebe appreciated that, in the preparation of the agents which are utilizedfor the purposes of the present invention, the various higher fattyacids or the like, hydroxyl-alkyl amines andcarboxylic acids containingnot more than five carbon atoms may be utilized in numerous combinationsand permutations tomalre large numbers of agents not specificallymentioned but the use of which is, nevertheless, within the scope of theinvention as pointed Out more particularly in the claims.

In general, most of the agents are prepared by initially reacting ahydroxy-alkyl amine containing hydrogen attached to nitrogen, andespecially a secondary hydroxy-alkyl amine, for example, diethanolamine,with an aliphatic carboxylic acid containing not more than five carbonatoms, or a derivative of such acid such as the halide or ester thereof,for example, acetic acid, acetic anhydride, acetyl chloride, ethylacetate or methyl acetate, under conditions such as assure a substantialyield of amide. The resulting amide is then reacted with a highermolecular weight organic acid or halide thereof or other lipophilecompound in order to introduce a lipophile radical into the molecule, ashereinafter more clearly set forth. The following examples areillustrative ofmethods which have been found suitable for preparingvarious of the dispersing agents which'are disclosed herein.

It will be appreciated that other methods may C. under a pressure of 6millimeters.

be utilized and that the proportions of reacting ingredients, times ofreaction, order oi. steps, and temperatures maybe varied and thatsupplementary processes of purification and the like may b resorted towherever found desirable or convenient.

in the art in the light of the guiding principles which are disclosedherein.

EXAMPLE A ('1) 224 grams of methyl acetate (3 mols) and 210 grams ofdiethanolamine (2 mols) were mixed together, two layers forming atfirst, the

- mixture becoming a homogeneous mass after a short time; The mixturewas refluxed for 19 hours at which time 90% of the diethanolamine hadreacted. vA portion of the reaction mixture was subjected to a vacuum of6 millimeters at 60 degrees C. in order to drive oi the volatilematerial, namely the unreacted methyl acetate and the methyl alcoholwhich was formed during the reaction. The residue, upon titration,showed a content of 4.64% of free. diethanolamine. To

192.5 grams of this residue, 34.! grams of methyl acetate were added andthe mixture was refluxed for 3 hours. The resulting reaction product wasthen freed from its low boiling constituents, namely, the methyl alcoholand unreacted methyl acetate, by maintaining the mass at 70 degrees Theresidue contained approximately 0.8% of unreacted diethanolamine, basedupon a determination of the alkalinity of said residue by titration. Theproduct was a light yellow colored syrup, solunolamine, having thefollowing formula:

' canon CHa-CN V O CrH40H (2) 51.0 grams (2 mols) of the acetic acidamide of diethanolamine, produced as described in part 1 hereof, and38.0 grams (1 mol) of lauric acid were heated together for 15 minutes atapproximately 200 degrees C., while passing carbon dioxide gas throughthe reaction mixture. At the end of the 15.minutes, the free lauric acidhad decreased to 1.3%. The product was a yellow colored syrup,dispersible in water and having good emulsifying and dispersingproperties. It could be salted out of its solution by the additionthereto of sodium chloride. The product consisted essentially of acompound having the following formula:

CHz-CN CzH4-0l]-CuH2i EXAMPLE B 21.1 grams of the acetic acid amide ofdiethanolamine, produced as described'in part 1 of Example Ahereinabove, and 20 grams of lauric acid were heated at 200 degrees C.for minutes, carbon dioxide gas being passed through the reactionmixture during the reaction in order to remove the water formed as aresult or the esterification. The product was a yellow oil, es-

sentially devoid of free fatty acid and freely dispersible in water. Ithad good emulsifying and dispersing properties. By the addition ofsodium chloride to the solution it could be salted out.

These and other variations andmodifications will become evident to thoseskilled The reaction product contained essentially the monolauric acidester of the acetic acid amide of diethanolamine.

Exsuru: C

(1) 156 grams of methyl lactate and 157.5 grams of diethanolamine wererefluxed for 3 hours at 94 degrees C., the alkalinity calculated asdiethanolamine dropping from 50.5% to 5.4%. To the reaction mass 78grams of methyl lactate were added and refluxing was continued for 3 and/2 hours at 95 degrees C. The alkalinity I dropped to 0.9% expressed asdiethanolamine. The excess methyl lactate and the methyl alcohol whichformed during the reaction were removed by distillation at a pressure of10mm. and at a temperature up to about 120 degrees C. The reactionproduct was a reddish brown, water-soluble, somewhat viscous materialand comprised largely or. essentially the lactic acid amide ofdiethanolamine.

(2) 37.3 grams of the lactic acid amide ofdiethanolamine, produced inpart 1 hereof, and 9.8 grams of lauric acid were heated together to 60.

degrees C. whereupon a homogeneous solution resulted, and the heatingwas then continued for 20 minutes at 140 degrees C., for 20 minutes at150 degrees C., for '20 minutes at 170 degrees C. and for 15 minutes at180 degrees C. The reaction product was a reddish brown oil whichpossessed good emulsifying properties and which also foamed well even inacidified aqueous media.

' ble in water, and contained a compound which i was essentially theacetic acid amide of dietha- V The product contained a substantialproportion of the lauric acid mono-ester of the lactic acid amide ofdiethanolamine.

As Examples 6, 7, l5 and 20 show, the agents may also comprise highermolecular weight other derivatives. The higher molecular weight ethersmay be prepared, for example, by reacting a formulae may be derived fromvarious sources.

Among the sources may be mentioned acetic acid, acetoacetic acid, ethylacetate, methyl 'acetate, acetic anhydride, acetyl chloride, formic,acid, lactic acid, propionic acid, butyric acid, hydroxy-butyric acid,furoic acid, ketene, tartaric acid, succinic acid, 'maleic acid, fumaricacid, crotonic acid; trimethylol acetic acid, dimethylol malonic acid,and homologues thereof; and, in general, aliphatic carboxylic acids,their esters, anhydrides and acyl halides, and substitution derivativesof said acids such as hydroxy, hydroxyalkyl, and carboxylic derivatives,which contain not more than five carbon atoms. Of special utility inmost cases, for the purposes of the present invention, are acetic acid,its esters and halides.

The organic radical represented by R, in other words the lipophilegroup, in the various general formulae hereinabove may also be derivedfrom a plurality of sources among which may be mentioned, for example,straight chain and branched chain, saturated and unsaturated,carboxylic, aliphatic (including cycloaliphatic), fatty, aromatic,hydroaromatic, and araiiphatic acids including caprylic acid, capricacid, pimelic acid,

sebacic acid, behenic acid, arachidic acid, cerotic acid, erucic acid,melissic acid. stearic acid, oleic acid, ricinoleic acid, ricinelaidicacid, ricinostearolic acid, linoleic acid, linolenic acid, lauric acid,myristic acid, palmitic acid, mixtures of any two or more of the abovementioned acids or other acids, mixed higher fatty acids derived fromanimal or vegetable sources, for example,

lard, coconut oil, rapeseed oil, sesame oil, alm kernel oil, palm oil,olive oil, corn oil, cottonseed oil, sardine oil, tallow, soya bean oil,peanut oil,

castor oil, seal oils, whale oil, shark oil and other fish oils,partially or completely hydrogenated animal and vegetable oils such asthose mentioned; oxidized and/or polymerized higher fatty acids orhigher fatty acids :2 :rived from oxidized and/or polymerizedtriglyceride oils; acyloxy V carboxylic acids such as CnHa-C-O-CHrCOQHaraliphatic and aromatic acids such asphthalic acid, Twitchell fattyacids, naphthoic acid; naphthenic acids; hydroxy aromatic acids such ashydroxy naphthoic acids, and the like and substitution and, additionderivatives of the aforementioned acids, in particular, halogen additionand substitution derivatives. It will be understood that mixtures of anytwo or more of said acids may be employed if desired and it will also beappreciated that said acids may contain substituent groups such assulphate, sulphonlc,

' nitrile, thiocyanogen, carbonyl, amide, amine or substituted amine,halogen, ketone and other groups. The acids may be employed as such orin the form of derivatives thereof such as carboxylic acid acyl halides,esters and the like. of particular utility are the fatty acids or theiracyl halides containing at least twelve and preferably from sixteen toeighteen carbon atoms.-

1,3-propanedio1; diglycerol-amine'i hydroxylamine (HaN-OH) andderivatives thereof such as result from replacement of one aminehydrogen by an alkyl such as methyl, ethyl, propyl, butyl and the higherhomologues: hydmxy amines, particularly secondary hydroxy amines,derived from polylrvdric alcohols, including sugars and sugar alcoholssuch as dextrom, sucrose, sorbitol, mannitol and dulcitol,

and the like; 2amino-2-methyl-1,3-propanediol;

In those cases where higher molecular weight ethers of the amides of theliydroxy-alkyl amines are prepared, the higher molecular weight etherradical may be derived from alcoholates prepared from alcoholscorresponding to the higher molecular weight acids referred tohereinabove.

The hydroxy amines which are reacted with the acetic acid or the like toproduce the intermediate amide include, among others, by way of example,diethanolamine, dipropanolamine, dibutanolamine, dipentanolamine,dihexanolamine, 2-methylamino-propan-diol-1,3;l-phenylaminopropan-diol-2,3; 1-hydroxy-ethylamino-2,methoxy-propan-ol-3; 2-N-methylamino-propan-diol- 1,3; monoethanolmonopropanolamine, monoethanol monobutanolamine, glycerol mono-amines,namely, 1-amino-2,3-propanediol and 2-aminotrimethylol amino methane;Z-amino-Z-n-propyl- 1,3 propanediol; 2 amino- 2-isopropyl-1,3-propanediol; 2-amino-2-methyl-1,4-butanediol;2-amino-2-methyl-1,5-pentanediol; 2-amino-2-ethyl- 1,3-propanediol;2-amino-2-ethy1ol-L3-propanediol; 2-amino-2-methyl-1,6-hexanediol;l-amino- 1,1-dimethyl ethanol; trimethylol amino-methyl methane;trimethylol amino-methylol methane. The glycerol mono-amines and therelated hydroxy amines such as various of those disclosed hereinabovemay be prepared by various procedures and in different ways. Many ofthem are conveniently produced by nitrating paraflin hydrocarbons,substituting methylol groups for hydrogen on the carbons to which thenitro groups are attached, and then reducing the nitro groups to aminegroups. These amine groups may be further alkylated or otherwisesubstituted if desired. Polymerized non-tertiary hydroxy amines orpolymerized hydroxy amines containing hydrogen directly attached tonitrogen and prepared, for example, by polymerizing monoethanolamine ordiethanolamine or mixtures thereof, or other hydroxy amines such asthose mentioned hereinabove, particularly in the presence of a catalystsuch as sodium hydroxide or the like, may also be employed. Thepreparation of polymerized hydroxy amines is disclosed, for example, inUnited States Patent No. 2,178,173; and homologues and substitutionderivatives of the abovementioned hydroxy amines. Because of commercialand other considerations, diethanolamine is especially desirable. Itwill be understood that the hydron amines may be utilized in pure,impure or commercial form.

The especial utility of the agents described hereinabove for thepurposes of the present invention appears to result from a particularcoaction among the acetamide or similar amide group, the highermolecular weight acyl or alkyl group or the like, and the free hydroxylor similar group or groups, the combined result of which is to impartthe highly desirable characteristics which are found in said agents.While, as described hereinabove, the agents contain at least one free orunesteriiied hydroxy group as, for example, in the case of the aceticacid amide of the mono-lauric acid ester of diethanolamine, it may bepointed out that, in some instances, the hydroxy group may be replacedby such groups as amino, carboxyl, and the like, or the hydrogen of thehydroxyl group or groups may be replaced by acetyl, lactyl and similargroups. However,

the agents function much more satisfactorily with a free or unesterifledhydroxyl .group or agents described herein may be utilized are many innumber and of widely varying. character.

"Among such emulsions and dispersions, which may be of neutral, acid oralkaline character, are

those containing pyrethrum, derris, rotenone, and other analogousmaterials and employed for insecticidal, fungicidal, germicidal,mothprooflng, and disinfectant purposes; for cosmetic purposes such ascold creams, vanishing creams, shaving creams of the brushless andlathering type, hand lotions, tissue creams, anti-perspiration creams,and the like; for emulsions of essential oils; for medicinal andpharmaceutical emulsions such as those containing fat-soluble vitaminsas, for ex- I ample, vitamins A and D such as are present in fish liveroils, irradiated ergosterol and the like; for cutting, boring, ordrilling oil emulsions or emulsions used for wire drawing; for emulsionstextile fibres-and yarns made from cotton, wool, linen and the like aswell as the artificially produced fibresand fabrics such asrayonjcellulose acetates, cellulose propionates, cellulose ethersandsimilar artificial silk fabrics and silk and wool substitutes; forpolishes for furniture, automobiles, and also for boots and shoes; forsizing emulsions used in the textile and paper industries; for greasingand lubricating emulsions; for paint or oil-color emulsions anddispersions; for

the preparation of emulsions or dispersions of resins of various otherkinds and for various other uses such as abrasive polishes; bitumen,asphaltand pitch emulsions; wax emulsions of wax such as candellila wax,paraffin wax, carnauba wax, montan' wax and the like used for polishesand similar purposes; chlorinated rubber emulsions; resin and lacqueremulsions used for coating and impregnating purposes and preferably madein the presence of alkaline materials, such resins includingnitrocellulose resins,

alkyd resins, acrylic ester resins such as methylmethacrylate, ethylmethacrylate and the like, cellulose esters in general, urea-aldehyderesins, glyptal resins, petroleum resins, coumarone resins, vinyl,resins, and the like; so-called lecithin emulsions; emulsions withvolatile soland ,mineral origin; waxes such as paraiiin, carnauba,beeswax, montan wax and thelike: higher fatty acids and other highermolecular weight acids such as stearic acid and palmitic acid; lanolinor wool'grease, and numerous other materials ofthe character indicated.The term "oleaginous material,-as employed in the claims,

will be understood to encompass oils, fats, higher fatty acids andwaxes.

Those emulsions or dispersions which are made in the presence of orwhich contain an alkaline material such as soap, borax or the like areespecially satisfactory, representative examples being cosmetic creamformulae as hereinafter set forth. Where, however, soap or thelikeis'objectionable, the'agents hereinabove described may be used as thesole emulsifying or dispersing agents in the emulsions or dispersions.

The emulsions or dispersions may contain desired proportions of additionagents such as talc,

medicinal or antiseptic materials, pigments such as lamp-black and zincoxide; alkali metal phosphates such as pyrophosphates andtetraphosphates, sodium sulphate, alum, perborates such as sodiumperborate; hydrophilic gums such as pectin, gum tragacanth, karaya,locust bean,

gelatin, arabic, and glue; and solvents such as carbon tetrachloride,monoethyl ether of ethylene glycol, monobutyl ether of ethylene glycol,monoethyl and monobutyl ethers of diethylene glycol,

cyclohexanol, and the likefor scouring and other treatments of textilesor While, as pointed out, the agents described hereinabove may be usedas the sole. emulsifying or dispersing agents in emulsions ordispersions,

it is frequently desirable to utilize said agents, for example, the.mono-steario acid ester of the acetic acid amide of 'diethanolamine, inemulsions or dispersions together with known wetvents for dry cleaning;latex and natural and synthetic rubber dispersions; leather-treatingemulsions; emulsions having solvent properties for use in v cleaningpaint surfaces, metal surfaces, woodwork, and floor coverings such aslinoleum, rugs and the like, such emulsions frequently containing pineoil with or without oleic acid;

for emulsions in the pharmaceutical industry,

particularly for external use; for emulsion paints containing linseedoil, shellac, pigments and the like, and for numerous other emulsions.

As indicated hereinabove, the emulsions or dispersions may be preparedfrom water or aqueous media and water-repelling or hydrophobic subting,emulsifying and penetrating agents such as the higher molecular weight.alkyl sulphates,

phosphates, pyrophosphates and tetraphosphates as, for example, laurylsodium sulphate, myristyl I sodium pyrophosphate, cetyl sodiumtetraphosphate, octyl sodium sulphate, oleyl sodium sulphate, and the"like; higher molecular weight sulphonic acid derivatives such asv cetylsodium sulphonate and lauryl sodium sulphonate; sulphocarboxylic acidesters of higher molecular weight alcohols such as lauryl sodiumsulphoacetate, dioctyl sodium sulphosuccinate', dilauryl potassiumsulpho-glutarate, lauryl monoethanolamine sulphoacetate, and the like;sulphuric and sulphonic derivatives of condensation products ofalkylolamines and higher fatty acids; reaction products of phosphoric,pyrophosphoric, metaphosphoric, tetraphosphoric, and polyphosphoricacids with higher molecular weight alcohols:

Turkey-redoils; compounds of the type of isopropyl naphthalene sodiumsulphonate, other classes of wetting agents.

The following examples are illustrative of the preparation of emulsionsor dispersions-utilizing and the agents which have been describedhereinabove. It will be appreciated that various other emulsions ordispersions may be made, as previously pointed out in detail, and thatthe proportions of the various ingredients including the desired agentmay be varied within limits. These and other variations andmodifications will be evident to those skilled in the art in the lightof the guiding principles which are disclosed herein. All parts listedare by weightexcept where otherwiseindicated. v

stances such as oils and fats of animal. vegetable Acetic d amide ofmonopalmitic acid ester of diethcmnlamine Exmt: 111

Hand Lotion Parts Stearic acid 145 Triethanniarnine '13 Water 3750Alcohol 250- Mineral oi 250 Quince seed mncflage 172 Monoethyl ether 01diethanolamine 250 Lactic acid amide oi the monostearic acid ester oi!dipropanolamine '75 Eluurrnn IV Mineral oil emulsion Parts Mineral nil87 Triethanolamine oleate l2 Acetic acid amide oi the monolauric acidester of diethanolamine... 3 Water As desired Exmtr: V

Cutting oil Part8 Mineral oil 1 99 Triethanolamine oleate l2 Acetic acidamide of monostearic acid ester f of 2-amino-2-methyl-l,3-propanediol '3Water p 459 The proportions or the agents employed aria subject torelatively wide variation, the amount utilized being dependent upon thepotency oi the o darw aliphatic hydroxyainine co to the general formulaiaH/ wherein o R-E- is an aliphatic acyl-radical containing not morethan live carbon atoms, D .and M are organic radicals containing atleast two carbon atoms, R is an organic lipophile radical containing atleast eight carbon atoms, and z and w are small whole numbers.

2. A composition in the form or an emulsion or dispersion, comprisingwater, oieaginous material,

and a proportion of an amide ofa secondary aliphatic hydroxy-aminecorresponding to-the general formula p-o-ca" M-on wherein o sis analiphatic acyl radical containing not more than five carbon atoms, Damiss are organic radicals containing. at least .two carbon atoms,

and

is an aliphatic carboxylic acyl radicalcontaining at least eight carbonatoms.

3. A composition which is adapted to or emulsiiy on being admixed withaqueous materials, comprising .a water-repelling base inparticular agentselected. the specific character or the emulsion in which-itis.utilized, and the particular results desired. V 0.1% to 5.0%, basedupon theweight oi theologaginous or water-repelling constituent or con.-stituents, will be eflective for most, purposes but the amount may beincreased substantially. Since, however, good results are, in general,obtained when using the smaller percentages, it is preferred to do so,particularly in view of economic and other considerations. From 0.6% to1.5%, based on the weight of the oleaginous or water-repellingconstituent or constituents, will serve eiiectively in most cases. r

, What we claim as new and desire to protect by Letters Patent oi theUnited States is:

1. A composition in the form of an emulsion or dispersion, comprisingwater, a water-repelling material, and a proportion or an amide or asec- In general, from about eight carbon atoms, and

gredient and a proportion 01' an amide or a secondary aliphatichydroxy-amine corresponding to the general formula D- 0R')- RCN/ g M- onwherein is an aliphatic acyl radical containing notmroe than live carbonatoms, D and M!- are organic radicals containing at least two carbonatoms, R is an organic lipophil e radical containing at least numbers.

.4. A composition which is adapted to disperse or emulsiiy on beingadmixed with-aqueous materials, comprising oleaginous material as a baseingredient, and a proportion of anamide of a secondary aliphatichydro'xyamine corresponding to the general formula v i iiis an aliphaticacyl radical containing not more than the carbon atoms, 1) and H areorganic andgaresmallwhole radicals containing at least two carbon atoms.and

wherein alk is a member selected from the group consisting of alkylene,(alkylene-O-alkylene): and (alkylene-S-alkylenem where tand w are smallwhole numbers, and R is a lipophilic, aliphatic radical containingat'least eight carbon atoms.

6. A composition which is adapted to disperse or emulsify on beingadmixed with aqueous materials, comprising oleaginous material as a baseingredient, and a proportion of a chemical compoundcorresponding'to -thegeneral formula I I terial,,and a proportion of a chemical compoundcorresponding to the general formula II CHr-CHa-O-C-R" is a. fatty acidacyl radical'containing not more than five carbon atoms, and

(|J RII is a fatty acid acyl radical containing at least eight carbonatoms.

- 8. A composition which is adapted to disperse or emulsify on beingadmixed with aqueous materlals, comprising oleaginous material as a.base ingredient, and a proportion of a chemical compound correspondingto the generalformula wherein.

is a fatty acid acyl radical containing at least eight carbon atoms, andv and: are small whole numbers.

9. A composition in the form of an emulsion or dispersion,comprisingwater, oleaginous materlal, and a proportlon'of a chemicalcompound;

corresponding to the general formula Q cH. cH.).0d-R" Clix-C- OKs-(CH1)r-OH wherein is a fatty acid acyl eight carbon atoms, and v and z are"small whole numbers.

10. A composition in the form of an emulsion or dispersion, comprisingwater, oleaginous material, and a proportion of an amide of a secondarypolyamine with an aliphatic acid containing not more than five carbonatoms, said secondary polyamine containing at least two hydroxy-alkylradicals, the hydrogen of the hydroxyl group of only one of saidhydroxyalkyl radicals being .replaced by a lipophile radical containingat least eight carbon atoms.

11. A composition in the form of an emulsion or dispersion, comprisingwater, oleaginous material, and a proportion of an amide of a secondaryaliphatic di-hydroxy amine with a' carboxylic acid containing not morethan five carbon atoms, the hydrogen of only one hydroxy group of saidhydroxy amine being replaced by an aliphatic radical containing at leasteight'carbon atoms.

12. A composition in the form of an emulsion or dispersion, comprisingwater, oleaginous material, and a proportion of the acetic acid amide ofthe mono-stearic acid ester of diethanolamine.

' 13. A cosmetic preparation, inthe ,form of any emulsion of oleaginousand aqueous media, containing a proportion of an amide of a secondaryaliphatic hydroxy-amine corresponding to the general formula I is analiphatic acyl radical containing not more than five carbon atoms, D andM are organic radicals containing at least two carbon atoms,

' R is an organic lipophilev radical containing at least eight carbonatoms, and :c and y are small whole numbers.

14. A cosmetic preparation comprising an emulsion of oleaginous andaqueous materials, the oleaginous material comprising predominantly anormally solid higher molecular weight fatty acid, andcontaining aproportion of a chemical compound corresponding to the I general formularadical containing at least.

is a fatty acid acyl radcal containing at least eight carbon atoms, andv and z are small whole numbers.

15. A composition in theiorm of an emulsion or dispersion, comprisingwater, a waterrepelling material, and a proportion of an amide wot asecondary aliphatic hydroxy-amine with a carboxylic acid containing notmore than flve carbon atoms, the hydrogen of a hydroxy group of saidhydroxy-amine being replaced by an allphatic radical containing at leasteight carbon atoms, said amide containing at least one free hydroxygroup.

16. A composition which is adapted to disperse or emulsii'y on beingadmixed with aqueous materials, comprising oleaginous material as a baseingredient, and a proportion of a chemical compound in the form or anamide of an aliphatic hydroxy-amine with an aliphatic carboxylic acidcontaining not more than five carbon atoms, said chemical compound. alsoincluding at least one free hydroxy group and a higher molecular weightcarboxylic acyl radical having at least eight carbon atoms ester-linkedto an hydroxy group of the hvdroxy-amine.

17. A composition in the form of an emulsion or dispersion includingaqueous material and a proportion oi a compound in the form oi! an amideof an hydroxy-alkyl amine with a carboxylic acid containing not morethan flve carbon atoms, said compound also -containing at least one treehydroxy group and at least one lipophile group having at least eightcarbon atoms.

18. A composition which is adapted to disperse or emulsiiy on beingmixed with aqueous materials, comprising oleaginous material, and aproportion of a compound comprising an amide of a secondaryhydroxy-alkyl amine with an aliphatic carboxylic acid containing notmore than five carbon atoms, said compound also containing at least onefree hydroxyl group and at least one carboxylic acyl radical having atleast eight carbon atoms ester-linked to an hydroxy group or groups ofsaid hydroxy-alkyl amine. BENJAMIN R. HARRIS. FRANK J. CAHN.

